In this chapter, the authors argue for designing the context, not just the technology, of e-learning simulations (eSims). They examine the limitations of “pure” eSims (i.e., not involving human-delivered feedback) in light of design challenges for informal learning, and learning transfer, in today's knowledge-intensive work environment when solutions call for creative responses to messy, non-structured tasks in different organizational contexts. Authentic learning on realistic tasks is needed in the design of eSims in such situations. Neaman describes ways that directed performance support (DPS), an approach he pioneered, helps to overcome such limitations. He identifies a core set of DPS guidelines that others can use to adapt and utilize DPS designs in their eSimS. Using a system dynamics framework, Marsick discusses organizational barriers and supports that also need to be considered in eSim learning design for effective engagement and learning transfer.